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Vacation Tip: Where to Eat in Chicago

Apr 25, 2019 | Travel | 0 comments

A restaurant has to be really exceptional for me to give
it a five-star rating. Harry Caray’s Italian Steakhouse on West Kinzie was that
good. After a long day visiting the Shedd Aquarium and strolling around sunny Chicago,
we were all starving. The kids and I decided to try an early dinner at the
famous River North landmark. A sophisticated sports bar, with ties to Al Capone,
there is plenty of other interesting history behind the restaurant. Adored by
fans from near and far, Harry Caray was a famous sports announcer who ultimately
landed at Wrigley Field. There he became the voice of Chicago baseball, best known
for singing “Take Me Out to The Ball Game” during the 7th inning stretch
and exclaiming “Holy Cow!” He had a huge impact on the game and those who loved it.

The first indication that this was an above-average
restaurant was when we arrived fifteen minutes early for our reservation.
Rather than giving us a hard time or making us wait at the bar, the hostess
welcomed us with a smile and seated us instantly. When I saw the spotless white
tablecloths, beautifully set tables, and smart-looking waiters, I worried that
we were underdressed. If we were, our servers gave no indication that they
found our appearance lacking. The three of us were treated like royalty through
the entire meal.

We began with cocktails, a Navy Pier (Julia), a Cosmopolitan
(Calvin), and a glass of red wine (boring me!). Next, we ordered appetizers. We
shared sausage & peppers crostini, a colorful medley of fresh Italian
Sausage, red, green, and yellow peppers, and red onion with salsa verde on
garlic toast, and toasted ravioli-a mix of four cheese and Italian sausage
raviolis. Both were delicious.

Next it was time for the serious business-ordering the
meat that Harry Caray’s is renowned for. Our knowledgeable waiter explained
that most of the Midwestern beef is corn-fed (my personal favorite) and many
cuts can be ordered either dry or wet-aged for maximum tenderness and flavor.
Julia chose the wet-aged New York strip, Calvin the dry-aged Rib Eye, and I got
the Filet Mignon. We shared tastes and each one was fantastic. I was
particularly impressed with my perfectly-cooked medium rare cut, as that seems
to be the hardest for most chefs to master. Though the steaks can be requested
with “crusts” such as peppercorn or horseradish, we chose to go the purist
route so as to experience the full essence of the meats.

This is a quality over quantity restaurant, and the
entrees do not come with sides. However, we each ordered one. My BLT Wedge
salad was phenomenal-the ideal balance of cool, crisp iceberg lettuce,
Applewood bacon, and Roma tomatoes lightly drenched in bleu cheese dressing and
crumbled Gorgonzola. The ideal complement to my filet! Cal’s asparagus was
excellent too. Julia tried the bacon cheddar potato. It was delicious, but so
big she couldn’t possibly finish it, even with our help.

A review wouldn’t be complete without describing the
waitstaff. Everyone was outstanding. As with any extraordinary experience, it
was all in the details. The waiters were immaculately dressed and so
professional that Julia asked “Do they have to go to waiter school to work
here?” Though Cal and I laughed, it was true. Our water glasses were kept full
throughout the meal. Plates were removed at exactly the right moment, never too
quickly or after sitting in front of us for fifteen minutes. Our server was
informative, without lecturing or being condescending. Every single item we
ordered appeared hot, fresh, and in a timely manner. When we were finished, one
man even managed to produce a “crumb scraper” (aka table crumber) to clean off the
tablecloth for us, an old-fashioned gadget harkening back to earlier days that somehow
managed to be quite touching. At Harry Caray’s you are made to feel both like
an honored guest and completely at home, a delicate balance that few eating
establishments are able to achieve.

Harry Caray’s is not cheap, but this is a true
instance of “You get what you pay for.” I don’t regret a single penny spent.
The only regret I do have is that we didn’t save room for dessert. The table
next to us apparently knew better! When I saw their key lime pie and hot fudge
brownie sundae skillet, I vowed to return to this wonderful eatery the next
time I’m in the area!

Five stars!

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